So I found a couple of things to make those small paint jobs easier.
This Trim Paint kit I picked up at Home Depot is the first step...
This turkey baster is the next tool. Filling a small paint tray can get really messy! So I thought about how to fill it without drips. This is what I came up with and it works great!
Fill your baster from the can,
then fill the tray from the baster!
I actually filled it holding it over the can so no drips would escape if my aim wasn't great.
If you don't feel like cleaning the baster every time, you could just buy a few from the dollar store and toss it when done.